{(2S,3R,4S,6S)-4-Benzyloxy-6-[(2R,4R,6R)-6-((R)-2-hydroxy-1,1-dimethyl-but-3-enyl)-2-methoxy-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetaldehyde

Base Information

• Chemical Name: {(2S,3R,4S,6S)-4-Benzyloxy-6-[(2R,4R,6R)-6-((R)-2-hydroxy-1,1-dimethyl-but-3-enyl)-2-methoxy-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetaldehyde
• CAS No.: 215120-36-8
• Molecular Formula: C₂₉H₄₂O₇
• Molecular Weight: 502.648
• Mol file: 215120-36-8.mol

Synonyms:{(2S,3R,4S,6S)-4-Benzyloxy-6-[(2R,4R,6R)-6-((R)-2-hydroxy-1,1-dimethyl-but-3-enyl)-2-methoxy-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetaldehyde

Chemical Property of {(2S,3R,4S,6S)-4-Benzyloxy-6-[(2R,4R,6R)-6-((R)-2-hydroxy-1,1-dimethyl-but-3-enyl)-2-methoxy-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2S,3R,4S,6S)-4-Benzyloxy-6-[(2R,4R,6R)-6-((R)-2-hydroxy-1,1-dimethyl-but-3-enyl)-2-methoxy-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetaldehyde

There total 11 articles about {(2S,3R,4S,6S)-4-Benzyloxy-6-[(2R,4R,6R)-6-((R)-2-hydroxy-1,1-dimethyl-but-3-enyl)-2-methoxy-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

((2S,3R,4S,6S)-4-Benzyloxy-6-{(2R,4R,6R)-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl}-3-methyl-tetrahydro-pyran-2-yl)-acetaldehyde (215120-45-9) → {(2S,3R,4S,6S)-4-Benzyloxy-6-[(2R,4R,6R)-6-((R)-2-hydroxy-1,1-dimethyl-but-3-enyl)-2-methoxy-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetaldehyde (215120-36-8)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 2.5h;

DOI:10.1021/ja982431b

Reference yield:

((2S,3R,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester (162718-31-2) → {(2S,3R,4S,6S)-4-Benzyloxy-6-[(2R,4R,6R)-6-((R)-2-hydroxy-1,1-dimethyl-but-3-enyl)-2-methoxy-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetaldehyde (215120-36-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, from -78 deg C to 0 deg C

2: tetrahydrofuran / a) -78 deg C, 5 min, b) 20 deg C, 16 h

3: 92 percent / aq. TFA / tetrahydrofuran / 4.5 h / 20 °C

4: ZnI₂ / CH₂Cl₂ / 5.5 h / 20 °C

5: LiAlH₄ / tetrahydrofuran / 0 °C

6: imidazole / dimethylformamide / 0 °C

7: 93 percent / m-CPBA / CH₂Cl₂ / -60 °C

8: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 30 min

9: 65 percent / p-TsOH*H₂O, MeOH / 72 h / 25 °C

10: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, from -60 deg C to 0 deg C

11: 92 percent / DDQ / CH₂Cl₂ / 2.5 h / 20 °C

With 1H-imidazole; methanol; lithium aluminium tetrahydride; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja982431b

Reference yield:

[(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (215120-31-3) → {(2S,3R,4S,6S)-4-Benzyloxy-6-[(2R,4R,6R)-6-((R)-2-hydroxy-1,1-dimethyl-but-3-enyl)-2-methoxy-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetaldehyde (215120-36-8)

Guidance literature:

Multi-step reaction with 8 steps

1: ZnI₂ / CH₂Cl₂ / 5.5 h / 20 °C

2: LiAlH₄ / tetrahydrofuran / 0 °C

3: imidazole / dimethylformamide / 0 °C

4: 93 percent / m-CPBA / CH₂Cl₂ / -60 °C

5: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 30 min

6: 65 percent / p-TsOH*H₂O, MeOH / 72 h / 25 °C

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, from -60 deg C to 0 deg C

8: 92 percent / DDQ / CH₂Cl₂ / 2.5 h / 20 °C

With 1H-imidazole; methanol; lithium aluminium tetrahydride; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja982431b

upstream raw materials:

((2S,3R,4S,6S)-4-Benzyloxy-6-{(2R,4R,6R)-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl}-3-methyl-tetrahydro-pyran-2-yl)-acetaldehyde

((2S,3R,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

[(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

[(2S,3R,4S,6S)-4-Benzyloxy-6-((E)-2-methoxy-vinyl)-3-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Downstream raw materials:

{(2S,3R,4S,6S)-4-Benzyloxy-6-[(2R,4R,6R)-6-((R)-2-hydroxy-1,1-dimethyl-but-3-enyl)-2-methoxy-4-methyl-3-oxo-tetrahydro-pyran-2-ylmethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid

(1S,3R,5R,7R,9R,13S,14R,15S)-15-Benzyloxy-3-methoxy-5,8,8,14-tetramethyl-9-vinyl-10,17,18-trioxa-tricyclo[11.3.1.1^3,7]octadecane-4,11-dione

(1S,3R,5R,7R,9S,13S,14R,15S)-15-Benzyloxy-3-methoxy-5,8,8,14-tetramethyl-4,11-dioxo-10,17,18-trioxa-tricyclo[11.3.1.1^3,7]octadecane-9-carbaldehyde

(1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]actadecane